Epoxidation of cholesterol by hepatic microsomal lipid hydroperoxides
[1,2-3H]Cholesterol was epoxidized to radioactive cholesterol α- and β-epoxides (5,6α-epoxy-5α- and 5,6β-epoxy-5β-cholestan-3β-ols) in the ratio 1:4 by hepatic microsomal lipid hydroperoxides (MsOOH, 1 mM as active oxygen) in the presence of ferrous ion. MsOOH could be replaced by methyl linoleate h...
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| Veröffentlicht in: | Biochemical and biophysical research communications 1982-09, Vol.108 (2), p.724-730 |
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| container_title | Biochemical and biophysical research communications |
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| creator | Watabe, Tadashi Isobe, Masakazu Tsubaki, Atsushi |
| description | [1,2-3H]Cholesterol was epoxidized to radioactive cholesterol α- and β-epoxides (5,6α-epoxy-5α- and 5,6β-epoxy-5β-cholestan-3β-ols) in the ratio 1:4 by hepatic microsomal lipid hydroperoxides (MsOOH, 1 mM as active oxygen) in the presence of ferrous ion. MsOOH could be replaced by methyl linoleate hydroperoxides (MOOH) under the same conditions although the latter was less effective than the former. None of cumene hydroperoxide, t-butyl hydroperoxide, and hydrogen peroxide was an effective oxidant even at 10 mM. Neither ADP nor EDTA had an effect on the epoxidation of cholesterol by MsOOH as well as by MOOH. Ferrous ion could not be replaced by ferric ion in the hydroperoxide-mediated epoxidation. Cyanide anion potentially inhibited the reaction. |
| doi_str_mv | 10.1016/0006-291X(82)90889-0 |
| format | Article |
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MsOOH could be replaced by methyl linoleate hydroperoxides (MOOH) under the same conditions although the latter was less effective than the former. None of cumene hydroperoxide, t-butyl hydroperoxide, and hydrogen peroxide was an effective oxidant even at 10 mM. Neither ADP nor EDTA had an effect on the epoxidation of cholesterol by MsOOH as well as by MOOH. Ferrous ion could not be replaced by ferric ion in the hydroperoxide-mediated epoxidation. Cyanide anion potentially inhibited the reaction.</description><identifier>ISSN: 0006-291X</identifier><identifier>EISSN: 1090-2104</identifier><identifier>DOI: 10.1016/0006-291X(82)90889-0</identifier><identifier>PMID: 7150318</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Animals ; Cholesterol - analogs & derivatives ; Cholesterol - biosynthesis ; Cholesterol - metabolism ; Ferrous Compounds - pharmacology ; In Vitro Techniques ; Lipid Metabolism ; Male ; Microsomes, Liver - drug effects ; Microsomes, Liver - metabolism ; Peroxides - metabolism ; Rats ; Rats, Inbred Strains</subject><ispartof>Biochemical and biophysical research communications, 1982-09, Vol.108 (2), p.724-730</ispartof><rights>1982 Academic Press, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c423t-1e43d7cee0d192755d1c304e195c087c4519257ea4b88ffd6610d143f02feac23</citedby><cites>FETCH-LOGICAL-c423t-1e43d7cee0d192755d1c304e195c087c4519257ea4b88ffd6610d143f02feac23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0006-291X(82)90889-0$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7150318$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Watabe, Tadashi</creatorcontrib><creatorcontrib>Isobe, Masakazu</creatorcontrib><creatorcontrib>Tsubaki, Atsushi</creatorcontrib><title>Epoxidation of cholesterol by hepatic microsomal lipid hydroperoxides</title><title>Biochemical and biophysical research communications</title><addtitle>Biochem Biophys Res Commun</addtitle><description>[1,2-3H]Cholesterol was epoxidized to radioactive cholesterol α- and β-epoxides (5,6α-epoxy-5α- and 5,6β-epoxy-5β-cholestan-3β-ols) in the ratio 1:4 by hepatic microsomal lipid hydroperoxides (MsOOH, 1 mM as active oxygen) in the presence of ferrous ion. MsOOH could be replaced by methyl linoleate hydroperoxides (MOOH) under the same conditions although the latter was less effective than the former. None of cumene hydroperoxide, t-butyl hydroperoxide, and hydrogen peroxide was an effective oxidant even at 10 mM. Neither ADP nor EDTA had an effect on the epoxidation of cholesterol by MsOOH as well as by MOOH. Ferrous ion could not be replaced by ferric ion in the hydroperoxide-mediated epoxidation. Cyanide anion potentially inhibited the reaction.</description><subject>Animals</subject><subject>Cholesterol - analogs & derivatives</subject><subject>Cholesterol - biosynthesis</subject><subject>Cholesterol - metabolism</subject><subject>Ferrous Compounds - pharmacology</subject><subject>In Vitro Techniques</subject><subject>Lipid Metabolism</subject><subject>Male</subject><subject>Microsomes, Liver - drug effects</subject><subject>Microsomes, Liver - metabolism</subject><subject>Peroxides - metabolism</subject><subject>Rats</subject><subject>Rats, Inbred Strains</subject><issn>0006-291X</issn><issn>1090-2104</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1982</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF1LwzAUhoMoc07_gUKvRC-q56Rpm94IMuYHDLxR8C50ySmLtEtNOnH_3swNL70K5H3ek5OHsXOEGwQsbgGgSHmF71eSX1cgZZXCARsjVJByBHHIxn_IMTsJ4QMAURTViI1KzCFDOWazWe--rakH61aJaxK9dC2Fgbxrk8UmWVIfI510VnsXXFe3SWt7a5LlxnjXRyyWKZyyo6ZuA53tzwl7e5i9Tp_S-cvj8_R-nmrBsyFFEpkpNREYrHiZ5wZ1BoKwyjXIUos8Xucl1WIhZdOYosBIiqwB3lCteTZhl7u5vXef67in6mzQ1Lb1itw6KAkcpIA8gmIHbtcOnhrVe9vVfqMQ1Nae2qpRWzVKcvVrT0GsXeznrxcdmb_SXlfM73Y5xU9-WfIqaEsrTcZ60oMyzv7_wA_Xh38S</recordid><startdate>19820930</startdate><enddate>19820930</enddate><creator>Watabe, Tadashi</creator><creator>Isobe, Masakazu</creator><creator>Tsubaki, Atsushi</creator><general>Elsevier Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19820930</creationdate><title>Epoxidation of cholesterol by hepatic microsomal lipid hydroperoxides</title><author>Watabe, Tadashi ; Isobe, Masakazu ; Tsubaki, Atsushi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c423t-1e43d7cee0d192755d1c304e195c087c4519257ea4b88ffd6610d143f02feac23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1982</creationdate><topic>Animals</topic><topic>Cholesterol - analogs & derivatives</topic><topic>Cholesterol - biosynthesis</topic><topic>Cholesterol - metabolism</topic><topic>Ferrous Compounds - pharmacology</topic><topic>In Vitro Techniques</topic><topic>Lipid Metabolism</topic><topic>Male</topic><topic>Microsomes, Liver - drug effects</topic><topic>Microsomes, Liver - metabolism</topic><topic>Peroxides - metabolism</topic><topic>Rats</topic><topic>Rats, Inbred Strains</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Watabe, Tadashi</creatorcontrib><creatorcontrib>Isobe, Masakazu</creatorcontrib><creatorcontrib>Tsubaki, Atsushi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Biochemical and biophysical research communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Watabe, Tadashi</au><au>Isobe, Masakazu</au><au>Tsubaki, Atsushi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Epoxidation of cholesterol by hepatic microsomal lipid hydroperoxides</atitle><jtitle>Biochemical and biophysical research communications</jtitle><addtitle>Biochem Biophys Res Commun</addtitle><date>1982-09-30</date><risdate>1982</risdate><volume>108</volume><issue>2</issue><spage>724</spage><epage>730</epage><pages>724-730</pages><issn>0006-291X</issn><eissn>1090-2104</eissn><abstract>[1,2-3H]Cholesterol was epoxidized to radioactive cholesterol α- and β-epoxides (5,6α-epoxy-5α- and 5,6β-epoxy-5β-cholestan-3β-ols) in the ratio 1:4 by hepatic microsomal lipid hydroperoxides (MsOOH, 1 mM as active oxygen) in the presence of ferrous ion. MsOOH could be replaced by methyl linoleate hydroperoxides (MOOH) under the same conditions although the latter was less effective than the former. None of cumene hydroperoxide, t-butyl hydroperoxide, and hydrogen peroxide was an effective oxidant even at 10 mM. Neither ADP nor EDTA had an effect on the epoxidation of cholesterol by MsOOH as well as by MOOH. Ferrous ion could not be replaced by ferric ion in the hydroperoxide-mediated epoxidation. Cyanide anion potentially inhibited the reaction.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>7150318</pmid><doi>10.1016/0006-291X(82)90889-0</doi><tpages>7</tpages></addata></record> |
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| ispartof | Biochemical and biophysical research communications, 1982-09, Vol.108 (2), p.724-730 |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Animals Cholesterol - analogs & derivatives Cholesterol - biosynthesis Cholesterol - metabolism Ferrous Compounds - pharmacology In Vitro Techniques Lipid Metabolism Male Microsomes, Liver - drug effects Microsomes, Liver - metabolism Peroxides - metabolism Rats Rats, Inbred Strains |
| title | Epoxidation of cholesterol by hepatic microsomal lipid hydroperoxides |
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